Methanol → (4-{(R)-2-[4-(3-Chlorophenyl)-3-hydroxy-butyl]-6-oxo-piperidin-1-yl}-but-2-ynyloxy)-acetic acid methyl ester

HRID 349361ノート

反応式

HRID 349361 の反応式
[BH4-].[Na+].CO.[CH3:5][O:6][C:7](=[O:33])[CH2:8][O:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C@@H:15]1[CH2:21][CH2:22][C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:33])[CH2:8][O:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C@@H:15]1[CH2:21][CH2:22][CH:23]([OH:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67011018(4-{(R)-2-[4-(3-Chlorophenyl)-3-oxo-butyl]-6-oxo-piperidin-1-yl}-but-2-ynyloxy)-acetic acid methyl ester

生成物 1

HCID 69022861(4-{(R)-2-[4-(3-Chlorophenyl)-3-hydroxy-butyl]-6-oxo-piperidin-1-yl}-but-2-ynyloxy)-acetic acid methyl ester収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sodium borohydride (2 mg, 0.053 mmol) followed by MeOH (0.1 mL) was added to a solution of (4-{(R)-2-[4-(3-chlorophenyl)-3-oxo-butyl]-6-oxo-piperidin-1-yl}-but-2-ynyloxy)-acetic acid methyl ester (5 mg, 0.012 mmol) in CH2Cl2 (0.3 mL) at 0° C. After 10 min at 0° C. the reaction was quenched with aqueous HCl (0.25 M, 3 mL). The reaction mixture was extracted with CH2Cl2 (3×4 mL), then the combined extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→2% MeOH/CH2Cl2) afforded 4.6 mg (92%) of the title compound.

後処理

  1. customAfter 10 min at 0° C. the reaction was quenched with aqueous HCl (0.25 M, 3 mL)
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×4 mL)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→2% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-602c594a4acf452383202510a155c2b9
出典データセット
uspto-grants-2007_02
特許番号
US07179820B2

反応ノート

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